ArticleBioorganic & medicinal chemistry letters2014
Facile synthesis of SSR180575 and discovery of 7-chloro-N,N,5-trimethyl-4-oxo-3(6-[(18)F]fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide, a potent pyridazinoindole ligand for PET imaging of TSPO in cancer.
Article in Bioorganic & medicinal chemistry letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 25 citations in OpenAlex.
- Anti-inflammatory treatment confirms rsfMRI and TSPO PET as biomarkers of functional connectivity and neuroinflammation in rat contusion spinal cord injuries.Scientific reports · 2026Article
- TSPO Radioligands for Neuroinflammation: An Overview.Molecules (Basel, Switzerland) · 2024Review
- Spatiotemporal Dynamics of Neuroinflammation Relate to Behavioral Recovery in Rats with Spinal Cord Injury.Molecular imaging and biology · 2024Article
- Review
- Essential Principles and Recent Progress in the Development of TSPO PET Ligands for Neuroinflammation Imaging.Current medicinal chemistry · 2022Review
- A perspective on the radiopharmaceutical requirements for imaging and therapy of glioblastoma.Theranostics · 2021Review
- TSPO-targeted PET and Optical Probes for the Detection and Localization of Premalignant and Malignant Pancreatic Lesions.Clinical cancer research : an official journal of the American Association for Cancer Research · 2020Article
- The Current Role of Microfluidics in Radiofluorination Chemistry.Molecular imaging and biology · 2020Review
- A unified structural model of the mammalian translocator protein (TSPO).Journal of biomolecular NMR · 2019Article
- Preclinical Evaluation of a Novel TSPO PET Ligand 2-(7-Butyl-2-(4-(2-[Molecular imaging and biology · 2019Article
- [ACS medicinal chemistry letters · 2018Article
- Evaluation of TSPO PET Ligands [Molecular imaging and biology · 2017Article
- Determination and reduction of translocator protein (TSPO) ligand rs6971 discrimination.MedChemComm · 2017Article
- New structure-activity relationships of N-acetamide substituted pyrazolopyrimidines as pharmacological ligands of TSPO.Bioorganic & medicinal chemistry letters · 2016Article
- Preclinical TSPO Ligand PET to Visualize Human Glioma Xenotransplants: A Preliminary Study.PloS one · 2015Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
A novel synthesis of the translocator protein (TSPO) ligand 7-chloro-N,N,5-trimethyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide (SSR180575, 3) was achieved in four steps from commercially available starting materials. Focused structure-activity relationship development about the pyridazinoindole ring at the N3 position led to the discovery of 7-chloro-N,N,5-trimethyl-4-oxo-3(6-fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide (14), a novel ligand of comparable affinity. Radiolabeling with fluorine-18 ((18)F) yielded 7-chloro-N,N,5-trimethyl-4-oxo-3(6-[(18)F]fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide ([(18)F]-14) in high radiochemical yield and specific activity. In vivo studies of [(18)F]-14 revealed this agent as a promising probe for molecular imaging of glioma.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.